Very interesting.
Are you playing the files sequentially: I.e., 1 - 253, then the restart at 254?
--> Yes, sequentially, and alphabetically by song name.
What happens if the CD is played randomly (if you have that feature) - will all 342 files eventually play or does it restart whenever file/song "254" is selected? Even if "254" happens to be the first to play.
Probably would take a lot of listening to see if "random" makes a difference within your car player.
--> Besides taking a lot of listening time, it would require a lot of attention. I am retired and tend to take short trips rather than commute. Though this is an option I will have to consider.
Can you replicate the problem via a CD-RW disc?
--> Never occurred to me. Again, an option I will have to consider.
Then overwrite the "area files" with other songs but using the same .mp3 file names.
--> Ditto.
Wish I could provide a direct answer per se. Still quite intrigued and thinking out loud a bit.....
What make and model is the CD player in your Highlander?
--> As is typical with cars today, there is nothing to identify the make/model, and the car manuals only tell you how to operate it.
254 = 11111110 binary.
--> Maximum number of characters in a valid email address? or (old) file path limit? or characters in an Excel cell when merging? Or ???
Perhaps there is some unique sequence of bits being sent via the CD to the player causing the restart to be setup and execute.
--> Wouldn't removing and/or replacing songs in the 253 to 257 range violate the "unique sequence" concept.
E.g. with respect to a Sony Remote....
http/www.armory.com/~spcecdt/remote/sony.html
No "254" code listed per se. But the idea is to see if some such pattern is unique to and present on the problem CD that in turn affects your car CD player. If you can find the codes for your CD player that might be a key.
Depending on how much time you have and really wish to spend on figuring it out.
--> I've spent a lot of time on this already. I posted because I was out of reasonable ideas and was looking for a fresh approach. Actually one just occured to me. Test the disc(s) in my wife's 2011 RAV4 (Problem: She drives less than me and pays almost no attention to the music.)
Thanks for the suggestions.